{"id":"https://openalex.org/W2008801566","doi":"https://doi.org/10.2133/dmpk.20.282","title":"Repeated Glucuronidation at One Hydroxyl Group Leads to Structurally Novel Diglucuronides of Steroid Sex Hormones","display_name":"Repeated Glucuronidation at One Hydroxyl Group Leads to Structurally Novel Diglucuronides of Steroid Sex Hormones","publication_year":2005,"publication_date":"2005-01-01","ids":{"openalex":"https://openalex.org/W2008801566","doi":"https://doi.org/10.2133/dmpk.20.282","mag":"2008801566","pmid":"https://pubmed.ncbi.nlm.nih.gov/16141608"},"language":"en","primary_location":{"id":"doi:10.2133/dmpk.20.282","doi":"https://doi.org/10.2133/dmpk.20.282","is_oa":false,"landing_page_url":"https://doi.org/10.2133/dmpk.20.282","pdf_url":null,"source":{"id":"https://openalex.org/S185835163","display_name":"Drug Metabolism and Pharmacokinetics","issn_l":"1347-4367","issn":["1347-4367","1880-0920"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","ki-jl-1","medline","norway-1","poland-70","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320990","host_organization_name":"Elsevier BV","host_organization_lineage":["https://openalex.org/P4310320990"],"host_organization_lineage_names":["Elsevier BV"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Drug Metabolism and Pharmacokinetics","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5080631350","display_name":"Takahiro Murai","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Takahiro Murai","raw_affiliation_strings":["Drug Metabolism and Pharmacokinetics Research Laboratories, Sankyo Co., Ltd., Tokyko, Japan. tmurai@sankyo.co.jp","Drug Metabolism and Pharmacokinetics Research Laboratories, Sankyo Co., Ltd"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Drug Metabolism and Pharmacokinetics Research Laboratories, Sankyo Co., Ltd., Tokyko, Japan. tmurai@sankyo.co.jp","institution_ids":[]},{"raw_affiliation_string":"Drug Metabolism and Pharmacokinetics Research Laboratories, Sankyo Co., Ltd","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5077748877","display_name":"Haruo Iwabuchi","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Haruo Iwabuchi","raw_affiliation_strings":["Drug Metabolism and Pharmacokinetics Research Laboratories, Sankyo Co., Ltd"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Drug Metabolism and Pharmacokinetics Research Laboratories, Sankyo Co., Ltd","institution_ids":[]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5112214078","display_name":"Toshihiko Ikeda","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Toshihiko Ikeda","raw_affiliation_strings":["Drug Metabolism and Pharmacokinetics Research Laboratories, Sankyo Co., Ltd"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Drug Metabolism and Pharmacokinetics Research Laboratories, Sankyo Co., Ltd","institution_ids":[]}]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":3580,"currency":"USD","value_usd":3580},"apc_paid":null,"fwci":0.9535,"has_fulltext":false,"cited_by_count":17,"citation_normalized_percentile":{"value":0.69742268,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":96},"biblio":{"volume":"20","issue":"4","first_page":"282","last_page":"293"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10375","display_name":"Pharmacogenetics and Drug Metabolism","score":0.9937000274658203,"subfield":{"id":"https://openalex.org/subfields/3004","display_name":"Pharmacology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T10375","display_name":"Pharmacogenetics and Drug Metabolism","score":0.9937000274658203,"subfield":{"id":"https://openalex.org/subfields/3004","display_name":"Pharmacology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T13736","display_name":"Steroid Chemistry and Biochemistry","score":0.0020000000949949026,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10756","display_name":"Estrogen and related hormone effects","score":0.0007999999797903001,"subfield":{"id":"https://openalex.org/subfields/1310","display_name":"Endocrinology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/glucuronidation","display_name":"glucuronidation","score":0.9139999747276306},{"id":"https://openalex.org/keywords/sex-steroids","display_name":"sex steroids","score":0.8050000071525574},{"id":"https://openalex.org/keywords/androgens","display_name":"androgens","score":0.6679999828338623},{"id":"https://openalex.org/keywords/estrogen","display_name":"estrogen","score":0.996999979019165},{"id":"https://openalex.org/keywords/liver-microsomes","display_name":"liver microsomes","score":0.765999972820282},{"id":"https://openalex.org/keywords/udp-glucose","display_name":"UDP-glucose","score":0.32600000500679016},{"id":"https://openalex.org/keywords/michaelis-menten-kinetics","display_name":"Michaelis-Menten kinetics","score":0.7910000085830688},{"id":"https://openalex.org/keywords/drug-metabolism","display_name":"drug metabolism","score":0.3400000035762787}],"concepts":[{"id":"https://openalex.org/C2779907587","wikidata":"https://www.wikidata.org/wiki/Q14901439","display_name":"Glucuronidation","level":4,"score":0.845118522644043},{"id":"https://openalex.org/C87644729","wikidata":"https://www.wikidata.org/wiki/Q547502","display_name":"Microsome","level":3,"score":0.8159164190292358},{"id":"https://openalex.org/C2778656385","wikidata":"https://www.wikidata.org/wiki/Q414986","display_name":"Estrone","level":3,"score":0.747785747051239},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7126709818840027},{"id":"https://openalex.org/C2777335581","wikidata":"https://www.wikidata.org/wiki/Q409721","display_name":"Estriol","level":3,"score":0.5445705652236938},{"id":"https://openalex.org/C2779279991","wikidata":"https://www.wikidata.org/wiki/Q6058681","display_name":"Testosterone (patch)","level":2,"score":0.5420116186141968},{"id":"https://openalex.org/C2780902042","wikidata":"https://www.wikidata.org/wiki/Q177911","display_name":"Steroid","level":3,"score":0.5072514414787292},{"id":"https://openalex.org/C2779746161","wikidata":"https://www.wikidata.org/wiki/Q422469","display_name":"Androsterone","level":4,"score":0.480937659740448},{"id":"https://openalex.org/C2776683971","wikidata":"https://www.wikidata.org/wiki/Q411064","display_name":"Androstenedione","level":4,"score":0.4800737500190735},{"id":"https://openalex.org/C25642318","wikidata":"https://www.wikidata.org/wiki/Q1992532","display_name":"Incubation","level":2,"score":0.46342599391937256},{"id":"https://openalex.org/C2776524530","wikidata":"https://www.wikidata.org/wiki/Q4119721","display_name":"Microsoma","level":4,"score":0.4149516522884369},{"id":"https://openalex.org/C126322002","wikidata":"https://www.wikidata.org/wiki/Q11180","display_name":"Internal medicine","level":1,"score":0.3874354362487793},{"id":"https://openalex.org/C134018914","wikidata":"https://www.wikidata.org/wiki/Q162606","display_name":"Endocrinology","level":1,"score":0.3598148226737976},{"id":"https://openalex.org/C43617362","wikidata":"https://www.wikidata.org/wiki/Q170050","display_name":"Chromatography","level":1,"score":0.3364149332046509},{"id":"https://openalex.org/C2777911890","wikidata":"https://www.wikidata.org/wiki/Q62614","display_name":"Androgen","level":3,"score":0.3230815529823303},{"id":"https://openalex.org/C71315377","wikidata":"https://www.wikidata.org/wiki/Q11364","display_name":"Hormone","level":2,"score":0.2675320506095886},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.26637277007102966},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.23758631944656372},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.15603682398796082},{"id":"https://openalex.org/C71924100","wikidata":"https://www.wikidata.org/wiki/Q11190","display_name":"Medicine","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000882","descriptor_name":"Haplorhini","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D002853","descriptor_name":"Chromatography, Liquid","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D004285","descriptor_name":"Dogs","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D004970","descriptor_name":"Estrone","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004970","descriptor_name":"Estrone","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007700","descriptor_name":"Kinetics","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008862","descriptor_name":"Microsomes, Liver","qualifier_ui":"Q000201","qualifier_name":"enzymology","is_major_topic":false},{"descriptor_ui":"D008862","descriptor_name":"Microsomes, Liver","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D012739","descriptor_name":"Gonadal Steroid Hormones","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D012739","descriptor_name":"Gonadal Steroid Hormones","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013045","descriptor_name":"Species Specificity","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013058","descriptor_name":"Mass Spectrometry","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013739","descriptor_name":"Testosterone","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D013739","descriptor_name":"Testosterone","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D014453","descriptor_name":"Glucuronosyltransferase","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D014535","descriptor_name":"Uridine Diphosphate Glucuronic Acid","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020719","descriptor_name":"Glucuronides","qualifier_ui":"Q000096","qualifier_name":"biosynthesis","is_major_topic":true},{"descriptor_ui":"D020719","descriptor_name":"Glucuronides","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D020719","descriptor_name":"Glucuronides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D051381","descriptor_name":"Rats","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.2133/dmpk.20.282","doi":"https://doi.org/10.2133/dmpk.20.282","is_oa":false,"landing_page_url":"https://doi.org/10.2133/dmpk.20.282","pdf_url":null,"source":{"id":"https://openalex.org/S185835163","display_name":"Drug Metabolism and Pharmacokinetics","issn_l":"1347-4367","issn":["1347-4367","1880-0920"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","ki-jl-1","medline","norway-1","poland-70","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320990","host_organization_name":"Elsevier BV","host_organization_lineage":["https://openalex.org/P4310320990"],"host_organization_lineage_names":["Elsevier BV"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Drug Metabolism and Pharmacokinetics","raw_type":"journal-article"},{"id":"pmid:16141608","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/16141608","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Drug metabolism and pharmacokinetics","raw_type":"Comparative Study"}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Good health and well-being","id":"https://metadata.un.org/sdg/3","score":0.428600013256073}],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":24,"referenced_works":["https://openalex.org/W47169895","https://openalex.org/W1559484899","https://openalex.org/W1820732766","https://openalex.org/W1862868295","https://openalex.org/W1961309037","https://openalex.org/W1995727180","https://openalex.org/W1999410521","https://openalex.org/W2005358101","https://openalex.org/W2016876126","https://openalex.org/W2026660910","https://openalex.org/W2035356008","https://openalex.org/W2041558174","https://openalex.org/W2046250267","https://openalex.org/W2061919879","https://openalex.org/W2066476106","https://openalex.org/W2071498240","https://openalex.org/W2075188571","https://openalex.org/W2084196863","https://openalex.org/W2089744422","https://openalex.org/W2144208846","https://openalex.org/W2145327188","https://openalex.org/W2340083957","https://openalex.org/W2422816370","https://openalex.org/W3025870308"],"related_works":["https://openalex.org/W1965243622","https://openalex.org/W2236670923","https://openalex.org/W2412881288","https://openalex.org/W2066866681","https://openalex.org/W2035356008","https://openalex.org/W2022211310","https://openalex.org/W2101114038","https://openalex.org/W2072308384","https://openalex.org/W1767382354","https://openalex.org/W2045524161"],"abstract_inverted_index":{"Androgens":[0],"(androsterone,":[1],"dihydrotestosterone":[2],"and":[3,5,9,20,30,88,99,166],"testosterone)":[4],"estrogens":[6],"(estradiol,":[7],"estriol":[8],"estrone)":[10],"were":[11,34,52,103],"incubated":[12],"with":[13,45,159],"liver":[14,47,101,122,126,145],"microsomes":[15,102,127,146],"from":[16,94,139,154],"rats,":[17],"dogs,":[18],"monkeys":[19],"humans":[21],"in":[22,71,143],"the":[23,31,80,84,89,95,108,120,140],"presence":[24],"of":[25,83,86,91,114,134,136,163,170],"uridine":[26],"diphosphoglucuronic":[27],"acid":[28],"(UDPGA),":[29],"glucuronides":[32],"produced":[33,128],"structurally":[35,57],"characterized":[36],"by":[37],"liquid":[38],"chromatography-tandem":[39],"mass":[40],"spectrometry.":[41],"After":[42],"2-h":[43],"incubation":[44,96],"dog":[46,121,144],"microsomes,":[48,123],"all":[49],"substrates":[50],"tested":[51],"converted":[53],"(approximately":[54],"2-10%)":[55],"to":[56,66,106,110,156],"novel":[58],"diglucuronides,":[59],"where":[60],"two":[61],"glucuronosyl":[62],"groups":[63],"are":[64],"bound":[65],"a":[67,160,167],"single":[68],"hydroxyl":[69],"group":[70],"tandem.":[72],"Two-dimensional":[73],"nuclear":[74],"magnetic":[75],"resonance":[76],"spectroscopy":[77],"unambiguously":[78],"elucidated":[79],"chemical":[81],"structures":[82],"3-O-diglucuronide":[85,138],"estrone":[87,137],"17-O-diglucuronide":[90],"testosterone":[92],"isolated":[93],"mixture.":[97],"Monkey":[98],"human":[100],"also":[104],"found":[105],"have":[107],"activity":[109],"form":[111],"this":[112],"type":[113],"diglucuronide,":[115],"albeit":[116],"more":[117],"slowly":[118],"than":[119],"but":[124],"rat":[125],"no":[129],"detectable":[130],"diglucuronides.":[131],"The":[132],"rate":[133],"formation":[135],"corresponding":[141],"monoglucuronide":[142],"followed":[147],"classical":[148],"Michaelis-Menten":[149],"kinetics":[150],"at":[151],"substrate":[152],"concentrations":[153],"50":[155],"1000":[157],"microM,":[158],"K(m)":[161],"value":[162,169],"127.1":[164],"microM":[165],"V(max)":[168],"47.0":[171],"pmol/min/mg":[172],"protein.":[173]},"counts_by_year":[{"year":2023,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":2},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":2}],"updated_date":"2026-11-07T11:25:07.637180","created_date":"2016-06-24T00:00:00"}
